4-Aryl(benzyl)sulfonyl-2-chloro-5-polyfluoroalkyl-1,2,3-triazoles. The first monocyclic N-chloro-1,2,3-triazoles

Yu P. Bandera, O. S. Kanishchev, V. M. Timoshenko, S. A. But, A. M. Nesterenko, Yu G. Shermolovich

Research output: Contribution to journalArticle

10 Scopus citations

Abstract

Treatment of 4-aryl(benzyl)sulfonyl-5-polyfluoroalkyl-v-triazoles with NaOCl gave the 4-aryl(benzyl)-sulfonyl-2-chloro-5-polyfluoroalkyl-v-triazole derivatives which contain a chlorine atom only on the N(2) atom of the heterocycle. The structure of 2-chloro-5-(1,1,2,2,3,3-hexafluoropropyl)-4- (p-tolyl-sulfonyl)-2H-[1,2,3]triazole has been established by X-ray structural investigation. The presence of a highly polarized N-Cl bond with a positive halogen atom causes the N-chlorotriazoles to react with KCN and KF as strong acids to form the potassium salts of the triazoles and to form 4-arylsulfonyl-2-(2-chloro-1-ethoxyethyl)-5-polyfluoroalkyl-2H-[1,2,3]triazoles with vinyl ethyl ether. It was found that chlorination of 4-arylsulfonyl-5- polyfluoroalkyl-v-triazoles in the presence of KF gives 4-chloro-5- polyfluoroalkyl-2H-[1,2,3]triazoles.

Original languageEnglish (US)
Pages (from-to)1138-1147
Number of pages10
JournalChemistry of Heterocyclic Compounds
Volume43
Issue number9
DOIs
StatePublished - Sep 1 2007

Keywords

  • 1,1-dihydropolyfluoroalkyl sulfone
  • N-chlorotriazole
  • V-triazole
  • X-ay structural analysis

ASJC Scopus subject areas

  • Organic Chemistry

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    Bandera, Y. P., Kanishchev, O. S., Timoshenko, V. M., But, S. A., Nesterenko, A. M., & Shermolovich, Y. G. (2007). 4-Aryl(benzyl)sulfonyl-2-chloro-5-polyfluoroalkyl-1,2,3-triazoles. The first monocyclic N-chloro-1,2,3-triazoles. Chemistry of Heterocyclic Compounds, 43(9), 1138-1147. https://doi.org/10.1007/s10593-007-0175-x